Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615004076/ky3073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615004076/ky3073Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615004076/ky3073Isup3.cml |
CCDC reference: 1051389
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL (Bruker, 2008).
C20H21NO4 | F(000) = 720 |
Mr = 339.38 | Dx = 1.395 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.516 (3) Å | Cell parameters from 7019 reflections |
b = 14.796 (5) Å | θ = 2.4–28.8° |
c = 10.620 (3) Å | µ = 0.10 mm−1 |
β = 101.986 (4)° | T = 150 K |
V = 1616.3 (9) Å3 | Needle, pale yellow |
Z = 4 | 0.39 × 0.17 × 0.03 mm |
Bruker SMART APEX CCD diffractometer | 3306 independent reflections |
Radiation source: fine-focus sealed tube | 2468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ and ω scans | θmax = 26.4°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2009) | h = −13→13 |
Tmin = 0.650, Tmax = 0.997 | k = −18→18 |
23937 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.132 | All H-atom parameters refined |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0723P)2 + 0.074P] where P = (Fo2 + 2Fc2)/3 |
3306 reflections | (Δ/σ)max < 0.001 |
310 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 60 sec per frame. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.01598 (13) | 0.06160 (9) | 0.36706 (14) | 0.0336 (4) | |
O3 | 0.22930 (14) | 0.01051 (9) | 0.41434 (14) | 0.0354 (4) | |
O9 | 0.17222 (12) | 0.72123 (8) | 0.45030 (11) | 0.0239 (3) | |
O10 | −0.04453 (12) | 0.79326 (8) | 0.30532 (13) | 0.0280 (3) | |
N7 | 0.25961 (14) | 0.44323 (10) | 0.43049 (14) | 0.0221 (4) | |
C2 | 0.0985 (2) | −0.01444 (14) | 0.3572 (2) | 0.0343 (5) | |
H2A | 0.0936 (18) | −0.0300 (14) | 0.259 (2) | 0.031 (5)* | |
H2B | 0.073 (2) | −0.0622 (16) | 0.405 (2) | 0.042 (6)* | |
C3A | 0.22800 (19) | 0.10373 (12) | 0.41602 (18) | 0.0268 (4) | |
C4 | 0.33017 (19) | 0.16167 (13) | 0.44905 (18) | 0.0272 (4) | |
H4 | 0.425 (2) | 0.1429 (13) | 0.4669 (19) | 0.035 (6)* | |
C4A | 0.30206 (18) | 0.25497 (13) | 0.45153 (17) | 0.0238 (4) | |
C5 | 0.41270 (19) | 0.32064 (14) | 0.4927 (2) | 0.0287 (5) | |
H5A | 0.461 (2) | 0.3298 (15) | 0.426 (2) | 0.039 (6)* | |
H5B | 0.479 (2) | 0.2963 (13) | 0.563 (2) | 0.033 (6)* | |
C6 | 0.36381 (18) | 0.40983 (13) | 0.5335 (2) | 0.0262 (4) | |
H6A | 0.4355 (16) | 0.4541 (12) | 0.5470 (17) | 0.017 (5)* | |
H6B | 0.3344 (18) | 0.4026 (13) | 0.617 (2) | 0.026 (5)* | |
C8 | 0.22941 (18) | 0.53680 (12) | 0.4588 (2) | 0.0242 (4) | |
H8A | 0.3083 (19) | 0.5739 (15) | 0.452 (2) | 0.036 (6)* | |
H8B | 0.2145 (17) | 0.5424 (13) | 0.5490 (19) | 0.024 (5)* | |
C8A | 0.10988 (16) | 0.57312 (12) | 0.37059 (17) | 0.0212 (4) | |
C9 | 0.08419 (17) | 0.66546 (12) | 0.37020 (17) | 0.0219 (4) | |
C10 | −0.02979 (18) | 0.70131 (12) | 0.29698 (17) | 0.0226 (4) | |
C11 | −0.11958 (18) | 0.64397 (13) | 0.22179 (18) | 0.0255 (4) | |
H11 | −0.2030 (19) | 0.6661 (13) | 0.1691 (19) | 0.028 (5)* | |
C12 | −0.09305 (18) | 0.55190 (13) | 0.22067 (18) | 0.0251 (4) | |
H12 | −0.1505 (19) | 0.5118 (13) | 0.1677 (19) | 0.029 (5)* | |
C12A | 0.01994 (17) | 0.51544 (12) | 0.29443 (17) | 0.0223 (4) | |
C13 | 0.04806 (19) | 0.41507 (12) | 0.29529 (19) | 0.0254 (4) | |
H13A | 0.0904 (17) | 0.3990 (13) | 0.216 (2) | 0.028 (5)* | |
H13B | −0.0306 (19) | 0.3836 (13) | 0.2815 (19) | 0.029 (5)* | |
C13A | 0.14229 (17) | 0.38655 (12) | 0.41905 (18) | 0.0225 (4) | |
H13C | 0.1002 (19) | 0.3994 (14) | 0.499 (2) | 0.039 (6)* | |
C13B | 0.17429 (17) | 0.28614 (12) | 0.41996 (17) | 0.0215 (4) | |
C14 | 0.07047 (18) | 0.22417 (12) | 0.38865 (18) | 0.0244 (4) | |
H14 | −0.023 (2) | 0.2423 (14) | 0.3727 (19) | 0.033 (6)* | |
C14A | 0.10102 (18) | 0.13438 (12) | 0.38828 (18) | 0.0257 (4) | |
C15 | 0.2498 (2) | 0.77260 (14) | 0.3804 (2) | 0.0272 (5) | |
H15A | 0.3058 (19) | 0.7324 (14) | 0.3347 (19) | 0.030 (5)* | |
H15B | 0.313 (2) | 0.8061 (16) | 0.440 (2) | 0.049 (7)* | |
H15C | 0.1959 (18) | 0.8084 (13) | 0.3141 (19) | 0.024 (5)* | |
C16 | −0.1724 (2) | 0.82776 (15) | 0.2625 (2) | 0.0320 (5) | |
H16A | −0.199 (2) | 0.8207 (15) | 0.172 (2) | 0.040 (6)* | |
H16B | −0.234 (2) | 0.7982 (15) | 0.311 (2) | 0.046 (7)* | |
H16C | −0.167 (2) | 0.8946 (16) | 0.283 (2) | 0.038 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0357 (8) | 0.0156 (7) | 0.0466 (9) | −0.0020 (6) | 0.0016 (7) | −0.0014 (6) |
O3 | 0.0438 (9) | 0.0155 (7) | 0.0424 (9) | 0.0039 (6) | −0.0016 (7) | 0.0015 (6) |
O9 | 0.0281 (7) | 0.0195 (7) | 0.0224 (7) | −0.0054 (5) | 0.0010 (5) | −0.0020 (5) |
O10 | 0.0313 (7) | 0.0163 (7) | 0.0340 (8) | 0.0037 (5) | 0.0010 (6) | 0.0012 (6) |
N7 | 0.0207 (8) | 0.0176 (8) | 0.0252 (8) | 0.0000 (6) | −0.0014 (6) | 0.0002 (6) |
C2 | 0.0428 (12) | 0.0173 (10) | 0.0401 (13) | 0.0012 (9) | 0.0021 (10) | −0.0018 (9) |
C3A | 0.0382 (11) | 0.0154 (9) | 0.0249 (10) | 0.0035 (8) | 0.0019 (8) | 0.0020 (8) |
C4 | 0.0284 (10) | 0.0256 (10) | 0.0258 (10) | 0.0050 (8) | 0.0015 (8) | 0.0037 (9) |
C4A | 0.0271 (10) | 0.0212 (10) | 0.0221 (10) | 0.0029 (8) | 0.0027 (8) | 0.0020 (8) |
C5 | 0.0239 (10) | 0.0251 (11) | 0.0341 (12) | 0.0017 (8) | −0.0012 (9) | 0.0039 (9) |
C6 | 0.0247 (10) | 0.0220 (10) | 0.0288 (11) | −0.0003 (8) | −0.0014 (8) | 0.0018 (8) |
C8 | 0.0248 (10) | 0.0174 (9) | 0.0276 (11) | −0.0018 (8) | −0.0012 (8) | −0.0024 (8) |
C8A | 0.0224 (9) | 0.0201 (9) | 0.0202 (9) | −0.0003 (7) | 0.0025 (7) | 0.0008 (8) |
C9 | 0.0235 (9) | 0.0198 (9) | 0.0214 (9) | −0.0039 (7) | 0.0022 (7) | −0.0010 (8) |
C10 | 0.0290 (10) | 0.0171 (9) | 0.0219 (9) | 0.0023 (7) | 0.0057 (8) | 0.0023 (7) |
C11 | 0.0252 (10) | 0.0242 (10) | 0.0251 (10) | 0.0015 (8) | 0.0004 (8) | 0.0046 (8) |
C12 | 0.0256 (10) | 0.0231 (10) | 0.0237 (10) | −0.0029 (8) | −0.0015 (8) | −0.0010 (8) |
C12A | 0.0253 (9) | 0.0189 (9) | 0.0216 (9) | −0.0003 (7) | 0.0025 (7) | 0.0001 (8) |
C13 | 0.0254 (10) | 0.0167 (9) | 0.0296 (11) | 0.0004 (8) | −0.0047 (8) | −0.0020 (8) |
C13A | 0.0220 (9) | 0.0173 (9) | 0.0268 (10) | −0.0012 (7) | 0.0016 (8) | −0.0011 (8) |
C13B | 0.0253 (9) | 0.0195 (9) | 0.0186 (9) | 0.0014 (7) | 0.0019 (7) | 0.0004 (7) |
C14 | 0.0251 (10) | 0.0204 (10) | 0.0264 (10) | 0.0015 (8) | 0.0022 (8) | 0.0017 (8) |
C14A | 0.0306 (10) | 0.0206 (10) | 0.0243 (10) | −0.0039 (8) | 0.0019 (8) | −0.0006 (8) |
C15 | 0.0289 (11) | 0.0236 (11) | 0.0270 (11) | −0.0054 (9) | 0.0014 (9) | 0.0016 (9) |
C16 | 0.0360 (12) | 0.0234 (11) | 0.0323 (12) | 0.0096 (9) | −0.0031 (9) | 0.0030 (9) |
O1—C14A | 1.388 (2) | C8—H8A | 1.01 (2) |
O1—C2 | 1.438 (2) | C8—H8B | 1.005 (19) |
O3—C3A | 1.379 (2) | C8A—C9 | 1.393 (3) |
O3—C2 | 1.431 (3) | C8A—C12A | 1.400 (2) |
O9—C9 | 1.391 (2) | C9—C10 | 1.391 (2) |
O9—C15 | 1.430 (2) | C10—C11 | 1.391 (3) |
O10—C10 | 1.374 (2) | C11—C12 | 1.391 (3) |
O10—C16 | 1.422 (2) | C11—H11 | 0.99 (2) |
N7—C6 | 1.464 (2) | C12—C12A | 1.389 (3) |
N7—C8 | 1.466 (2) | C12—H12 | 0.94 (2) |
N7—C13A | 1.476 (2) | C12A—C13 | 1.514 (2) |
C2—H2A | 1.06 (2) | C13—C13A | 1.532 (3) |
C2—H2B | 0.94 (2) | C13—H13A | 1.06 (2) |
C3A—C4 | 1.362 (3) | C13—H13B | 0.93 (2) |
C3A—C14A | 1.383 (3) | C13A—C13B | 1.523 (2) |
C4—C4A | 1.413 (3) | C13A—H13C | 1.05 (2) |
C4—H4 | 1.01 (2) | C13B—C14 | 1.411 (3) |
C4A—C13B | 1.394 (3) | C14—C14A | 1.367 (3) |
C4A—C5 | 1.509 (3) | C14—H14 | 1.00 (2) |
C5—C6 | 1.512 (3) | C15—H15A | 1.03 (2) |
C5—H5A | 0.96 (2) | C15—H15B | 0.96 (2) |
C5—H5B | 0.98 (2) | C15—H15C | 0.97 (2) |
C6—H6A | 0.987 (18) | C16—H16A | 0.95 (2) |
C6—H6B | 1.00 (2) | C16—H16B | 1.01 (2) |
C8—C8A | 1.503 (2) | C16—H16C | 1.01 (2) |
C14A—O1—C2 | 103.91 (15) | O10—C10—C9 | 115.91 (16) |
C3A—O3—C2 | 104.61 (14) | O10—C10—C11 | 124.64 (16) |
C9—O9—C15 | 112.13 (14) | C9—C10—C11 | 119.45 (17) |
C10—O10—C16 | 116.53 (15) | C12—C11—C10 | 119.25 (17) |
C6—N7—C8 | 109.01 (14) | C12—C11—H11 | 118.2 (12) |
C6—N7—C13A | 110.66 (14) | C10—C11—H11 | 122.5 (12) |
C8—N7—C13A | 109.92 (14) | C12A—C12—C11 | 121.67 (17) |
O3—C2—O1 | 107.99 (16) | C12A—C12—H12 | 117.3 (12) |
O3—C2—H2A | 108.7 (11) | C11—C12—H12 | 121.0 (12) |
O1—C2—H2A | 109.6 (11) | C12—C12A—C8A | 119.03 (17) |
O3—C2—H2B | 108.7 (13) | C12—C12A—C13 | 121.83 (16) |
O1—C2—H2B | 107.9 (14) | C8A—C12A—C13 | 119.14 (16) |
H2A—C2—H2B | 113.9 (18) | C12A—C13—C13A | 111.48 (15) |
C4—C3A—O3 | 128.55 (17) | C12A—C13—H13A | 109.2 (11) |
C4—C3A—C14A | 121.57 (17) | C13A—C13—H13A | 108.5 (10) |
O3—C3A—C14A | 109.69 (16) | C12A—C13—H13B | 108.8 (12) |
C3A—C4—C4A | 117.56 (17) | C13A—C13—H13B | 113.0 (12) |
C3A—C4—H4 | 124.6 (11) | H13A—C13—H13B | 105.6 (16) |
C4A—C4—H4 | 117.8 (11) | N7—C13A—C13B | 111.97 (15) |
C13B—C4A—C4 | 120.90 (17) | N7—C13A—C13 | 107.14 (15) |
C13B—C4A—C5 | 120.22 (17) | C13B—C13A—C13 | 112.15 (15) |
C4—C4A—C5 | 118.86 (16) | N7—C13A—H13C | 108.4 (11) |
C4A—C5—C6 | 110.94 (16) | C13B—C13A—H13C | 107.5 (12) |
C4A—C5—H5A | 111.9 (13) | C13—C13A—H13C | 109.6 (11) |
C6—C5—H5A | 110.6 (13) | C4A—C13B—C14 | 120.10 (17) |
C4A—C5—H5B | 111.7 (12) | C4A—C13B—C13A | 121.66 (16) |
C6—C5—H5B | 109.3 (12) | C14—C13B—C13A | 118.23 (16) |
H5A—C5—H5B | 102.0 (17) | C14A—C14—C13B | 117.47 (17) |
N7—C6—C5 | 109.04 (16) | C14A—C14—H14 | 119.0 (12) |
N7—C6—H6A | 108.4 (10) | C13B—C14—H14 | 123.4 (12) |
C5—C6—H6A | 109.0 (10) | C14—C14A—C3A | 122.36 (17) |
N7—C6—H6B | 112.1 (11) | C14—C14A—O1 | 127.64 (17) |
C5—C6—H6B | 110.2 (11) | C3A—C14A—O1 | 109.95 (16) |
H6A—C6—H6B | 108.1 (15) | O9—C15—H15A | 112.4 (11) |
N7—C8—C8A | 113.50 (15) | O9—C15—H15B | 108.8 (14) |
N7—C8—H8A | 106.5 (12) | H15A—C15—H15B | 103.1 (17) |
C8A—C8—H8A | 110.9 (12) | O9—C15—H15C | 111.0 (11) |
N7—C8—H8B | 110.9 (11) | H15A—C15—H15C | 106.3 (16) |
C8A—C8—H8B | 106.8 (10) | H15B—C15—H15C | 114.9 (18) |
H8A—C8—H8B | 108.2 (16) | O10—C16—H16A | 110.4 (13) |
C9—C8A—C12A | 119.28 (16) | O10—C16—H16B | 110.4 (13) |
C9—C8A—C8 | 119.31 (15) | H16A—C16—H16B | 112.3 (19) |
C12A—C8A—C8 | 121.31 (16) | O10—C16—H16C | 105.8 (12) |
O9—C9—C10 | 120.16 (16) | H16A—C16—H16C | 108.3 (19) |
O9—C9—C8A | 118.43 (15) | H16B—C16—H16C | 109.3 (18) |
C10—C9—C8A | 121.32 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O10i | 0.94 (2) | 2.58 (2) | 3.212 (3) | 124.5 (17) |
C16—H16A···O9ii | 0.95 (2) | 2.53 (2) | 3.455 (3) | 162.9 (18) |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+3/2, z−1/2. |